What it’s like to work for Rahm Emanuel

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  Emanuel's young staffers: Mike Simmons, from left, Ankur Thakkar, Caroline Weisser, Matt Fischler, Anna Valencia and Michael Faulman

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  Ankur Thakkar and Caroline Weisser talk in the press room at the mayor's office.

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  Ankur Thakkar and Caroline Weisser talk in the press room at the mayor's office.

   

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  Ankur Thakkar (from left), Anna Valencia and Caroline Weisser in the mayor's office

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  Staffers from the mayor's office exit through the front door.

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  Caroline Weisser (from left), Matt Fischler, Anna Valencia and Ankur Thakkar walk through Daley Plaza.

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  Matt Fischler (left) and Mike Simmons discuss city policies in Simmons's office in City Hall.

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  Michael Faulman (from left), Anna Valencia and Mike Simmons

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  Caroline Weisser (from left), Matt Fischler, Anna Valencia and Ankur Thakkar on a coffee break

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  Matt Fischler at an informal meeting with one of his colleagues at City Hall.

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  Mike Simmons (left) with Michael Faulman at City Hall

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  Mike Simmons (left) and Michael Faulman at City Hall

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  Mike Simmons (from left), Caroline Weisser, Matt Fischler and Michael Faulman 

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  A portrait of Mayor Rahm Emanuel hangs in a hallway at City Hall.

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  Ankur Thakkar (left) and Matt Fischler lend support while the mayor makes a major announcement about introducing Chicago's new Welcoming City Ordinance.

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  Ankur Thakkar checks the Twitter chatter as the mayor announces the upcoming introduction of the Welcoming City Ordinance.

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  Matt Fischler and Ankur Thakkar provide feedback to Chicago Office of New Americans Director Adolfo Hernandez post-event, where the mayor announced the new Welcoming Chicago Ordinance.

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  Anna Valencia waits while the mayor discusses an upcoming announcement on immigration with Chicago aldermen and U.S. Rep. Luis Gutierrez.

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  Caroline Weisser works behind the scenes during a press announcement aimed at investing in infrastructure and rennovating CTA facilities.

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  Newspaper clipping of Rahm Emanuel hang on the wall in Caroline Weisser's office at City Hall.

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Emanuel's young staffers: Mike Simmons, from left, Ankur Thakkar, Caroline Weisser, Matt Fischler, Anna Valencia and Michael Faulman

Photo: Elizabeth Jochum

IT’S AN 80-DEGREE JULY NIGHT AND cicadas are buzzing in the trees. Weisser and I are standing in Union Park, watching the mayor’s office softball team, the Four Stars, warm up for a game against the governor’s team, the Quinners. Thakkar rides up to the field on his bike wearing the Four Stars’ jersey: their namesake four-starred Chicago flag on the front and a number five on the back, for the mayor’s floor in City Hall. After waiting in vain for more female players to arrive (they need at least two), the Four Stars have to forfeit and play for fun.

Thakkar takes the field with Derek Lindblom, chief of staff of the mayor’s economic council, and Jacob Ringer, chief of staff to the city’s chief financial officer. Thakkar misses a pop-up foul and laughs sheepishly. Lindblom grabs him on the shoulder to say it’s okay, before throwing a ball that flies high over Thakkar’s head at third base. “[That play] was really egregious,” Ringer teases Lindblom later.

The Four Stars are down by several runs. They get a few base hits, then Tom Alexander, assistant press secretary, hits a grand slam. In true mayoral fashion—an Emanuel mantra is “Don’t spike the ball on the 15-yard line”—the Four Stars keep up the pace, winning by four, even though the score doesn’t count. They smile briefly at one another, say their good-byes quickly and head home to rest up for another day at City Hall. It’s not so different from how Valencia describes wins in the mayor’s office: “Once we hit an accomplishment, get back to work because there’s more to get done.”